methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

Base Information

Chemical Name:methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate
CAS No.:889670-04-6
Molecular Formula:C₂₈H₃₇NO₅Si
Molecular Weight:495.691
Hs Code.:

Synonyms:methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

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Chemical Property of methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

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Technology Process of methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

There total 2 articles about methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

: 170848-34-7,889670-02-4
methyl 2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate

: 889670-03-5
tert-butyl[(3-iodo-2-propynyl)oxy]diphenylsilane

: 889670-04-6
methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

Guidance literature:: methyl 2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 20 - 30 ℃; for 0.75h;

With lithium chloride; In tetrahydrofuran; at -10 ℃; for 0.2h;

tert-butyl[(3-iodo-2-propynyl)oxy]diphenylsilane; In tetrahydrofuran; at 20 ℃; for 20h;
DOI:10.1021/jo060349q

Reference yield:

: 88159-06-2
tert-butyl(diphenyl)(2-propynyloxy)silane

: 889670-04-6
methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 96 percent / iodine / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

2.1: 1,2-dibromoethane; TMSCl; zinc / tetrahydrofuran / 0.75 h / 20 - 30 °C

2.2: lithium chloride; CuCN / tetrahydrofuran / 0.2 h / -10 °C

2.3: 68 percent / tetrahydrofuran / 20 h / 20 °C

With n-butyllithium; chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; hexane;
DOI:10.1021/jo060349q

Reference yield:

: 889670-04-6
methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate

: tert-butyl (Z)-5-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)-3,4-dimethyl-3-pentenyl-carbamate

: [5-(tert-butyl-diphenyl-silanyloxy)-1-hydroxymethyl-pentyl]-carbamic acid tert-butyl ester

Guidance literature:: methyl 2-[(tert-butoxycarbonyl)amino]-6{[tert-butyl(diphenyl)silyl]oxy}-4-hexynoate; With hydrogen; palladium on barium sulfate; In ethyl acetate; Petroleum ether; for 10h;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 22h; Title compound not separated from byproducts;
DOI:10.1021/jo060349q